Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 15, Pages 3241-3246Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905774
Keywords
arenes; catalysis; C-H trifluoromethylation; electrophotochemistry; oxidant-free
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Funding
- DFG (Gottfried-Wilhelm-Leibniz award)
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Electrophotochemistry has enabled arene C-H trifluoromethylation with the Langlois reagent CF3SO2Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C-H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron-rich and electron-deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C-H trifluoromethylation was further achieved in flow with a modular electro-flow-cell equipped with an in-operando monitoring unit for on-line flow-NMR spectroscopy, providing support for the single electron transfer processes.
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